A metabolite-profiling approach allows the identification of new compounds from Pistacia lentiscus leaves

Journal of Pharmaceutical and Biomedical Analysis

Volumn 77, Issue , 2013, Pages 167-174

  Rodriguez Perez C ^a,b   Quirantes Pine R ^a,b   Amessis Ouchemoukh, N ^c   Khodir, M ^c   Segura Carretero, A ^a,b   Fernandez Gutierrez A ^a,b  

^a UNIVERSITY OF GRANADA   (Spain)

^b Functional Food Research and Development Center   (Spain)

^c UNIVERSITY OF BEJAIA   (Algeria)

Author keywords

HPLC DAD ESI MS; Metabolite profiling; Phenolic compounds; Pistacia lentiscus

Indexed keywords

ASTRAGALIN; BETA GLUCOGALLIN; CATECHIN; COUMARIC ACID; FLAVONOID; IRIDOID; KAEMPFEROL DERIVATIVE; LUTEOLIN; MYRICETIN; PISTACIA LENTISCUS EXTRACT; QUERCITRIN; QUERCITRIN GALLATE; QUINIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CONCENTRATION (PARAMETERS); DRUG IDENTIFICATION; DRUG RETENTION; LIMIT OF DETECTION; LIMIT OF QUANTITATION; LIPID METABOLISM; NONHUMAN; PISTACIA LENTISCUS; PLANT LEAF; PRIORITY JOURNAL;

CATECHIN; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLAVONOIDS; GLYCOSIDES; HYDROLYZABLE TANNINS; PHENOLS; PISTACIA; PLANT EXTRACTS; PLANT LEAVES; QUERCETIN; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 84874360931     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2013.01.026     Document Type: Article

References (45)

1. Jarić S., Mitrović M., Djurdjević L., Kostić O., Gajić G., Pavlović D., Pavlović P. Phytotherapy in medieval Serbian medicine according to the pharmacological manuscripts of the Chilandar Medical Codex (15-16th centuries). J. Ethnopharmacol. 2011, 137:601-619. 10.1016/j.jep.2011.06.016.
2. Paraschos S., Magiatis P., Gousia P., Economou V., Sakkas H., Papadopoulou C., Skaltsounis A.L. Chemical investigation and antimicrobial properties of mastic water and its major constituents. Food Chem. 2011, 129:907-911. 10.1016/j.foodchem.2011.05.043.
3. Trabelsi H., Cherif O.A., Sakouhi F., Villeneuve P., Renaud J., Barouh N., Boukhchina S., Mayer P. Total lipid content, fatty acids and 4-desmethylsterols accumulation in developing fruit of Pistacia lentiscus L. growing wild in Tunisia. Food Chem. 2012, 131:434-440. 10.1016/j.foodchem.2011.08.083.
4. Douissa F.B., Hayder N., Chekir-Ghedira L., Hammami M., Ghedira K., Mariotte A.M., Dijoux-Franca M.G. New study of the essential oil from leaves of Pistacia lentiscus L. (Anacardiaceae) from Tunisia. Flavour Fragrance J 2005, 20:410-414. 10.1002/ffj.1445.
5. Longo L., Platini F., Scardino A., Alabiso O., Vasapollo G., Tessitore L. Autophagy inhibition enhances anthocyanin-induced apoptosis in hepatocellular carcinoma. Mol. Cancer Ther. 2008, 7:2476-2485. 10.1158/1535-7163.MCT-08-0361.
6. Gioxari A., Kaliora A.C., Papalois A., Agrogiannis G., Triantafillidis J.K., Andrikopoulos N.K. Pistacia lentiscus resin regulates intestinal damage and inflammation in trinitrobenzene sulfonic acid-induced colitis. J Med. Food 2011, 14:1403-1411. 10.1089/jmf.2010.0240.
7. Markovics A., Cohen I., Muklada H., Glasser T.A., Dvash L., Ungar E.D., Azaizeh H., Landau S.Y. Consumption of Pistacia lentiscus foliage alleviates coccidiosis in young goats. Vet. Parasitol. 2011.
8. Piluzza G., Bullitta S. Correlations between phenolic content and antioxidant properties in twenty-four plant species of traditional ethnoveterinary use in the Mediterranean area. Pharm. Biol. 2011, 49:240-247. 10.3109/13880209.2010.501083.
9. Janakat S., Al-Merie H. Evaluation of hepatoprotective effect of Pistacia lentiscus, Phillyrea latifolia and Nicotiana glauca. J. Ethnopharmacol. 2002, 83:135-138. 10.1016/S0378-8741(02)00241-6.
10. Qiao J., Li A., Jin X., Wang J. Mastic alleviates allergic inflammation in asthmatic model mice by inhibiting recruitment of eosinophils. Am. J. Resp. Cell Mol. Biol. 2011, 45:95-100. 10.1165/rcmb.2010-0212OC.
11. Esmat A., Al-Abbasi F.A., Algandaby M.M., Moussa A.Y., Labib R.M., Ayoub N.A., Abdel-Naim A.B. Anti-inflammatory activity of pistacia khinjuk in different experimental models: isolation and characterization of its flavonoids and galloylated sugars. J Med. Food 2012, 15:278-287. 10.1089/jmf.2011.0099.
12. Cevallos-Cevallos J.M., Futch D.B., Shilts T., Folimonova S.Y., Reyes-De-Corcuera J.I. GC-MS metabolomic differentiation of selected citrus varieties with different sensitivity to citrus huanglongbing. Plant Physiol. Biochem. 2012, 53:69-76. 10.1016/j.plaphy.2012.01.010.
13. Fiehn O., Metabolomics The link between genotypes and phenotypes. Plant Mol. Biol. 2002, 48:155-171. 10.1023/A:1013713905833.
14. Harnly J.M., Bhagwat S., Lin L.Z. Profiling methods for the determination of phenolic compounds in foods and dietary supplements. Anal. Bioanal. Chem. 2007, 389:47-61. 10.1007/s00216-007-1424-7.
15. Romani A., Pinelli P., Galardi C., Mulinacci N., Tattini M. Identification and quantification of galloyl derivatives, flavonoid glycosides and anthocyanins in leaves of Pistacia lentiscus L. Phytochem. Anal. 2002, 13:79-86. 10.1002/pca.627.
16. Romier B., Schneider Y.J., Larondelle Y., During A. Dietary polyphenols can modulate the intestinal inflammatory response. Nutr. Rev. 2009, 67:363-378. 10.1111/j. 1753-4887.2009.00210.x.
17. Zeng Y., Song J.X., Shen X.C. Herbal remedies supply a novel prospect for the treatment of atherosclerosis: a review of current mechanism studies. Phytother. Res. 2012, 26:159-167. 10.1002/ptr.3587.
18. Kuroda M., Mimaki Y., Honda S., Tanaka H., Yokota S., Mae T. Phenolics from Glycyrrhiza glabra roots and their PPAR-(ligand-binding activity. Bioorg. Med. Chem. 2010, 18:962-970. 10.1016/j.bmc.2009.11.027.
19. Choi Y.W., Takamatsu S., Khan S.I., Srinivas P.V., Ferreira D., Zhao J., Khan I.A. Schisandrenea dibenzocyclooctadiene lignan from Schisandra chinensis: structure-antioxidant activity relationships of dibenzocyclooctadiene lignans. J. Nat. Prod. 2006, 69:356-359. 10.1021/np0503707.
20. Flores P., Hellín P., Fenoll J. Determination of organic acids in fruits and vegetables by liquid chromatography with tandem-mass spectrometry. Food Chem. 2012, 132:1049-1054. 10.1016/j.foodchem.2011.10.064.
21. Gómez-Romero M., Segura-Carretero A., Fernández-Gutiérrez A. Metabolite profiling and quantification of phenolic compounds in methanol extracts of tomato fruit. Phytochemistry 2010, 71:1848-1864. 10.1016/j.phytochem.2010.08.002.
22. Gao Q., Nilsson U., Ilag L.L., Leck C. Monosaccharide compositional analysis of marine polysaccharides by hydrophilic interaction liquid chromatography-tandem mass spectrometry. Anal. Bioanal. Chem. 2011, 399:2517-2529. 10.1007/s00216-010-4638-z.
23. Xiao C., Song Z.G., Liu Z.Q. Synthesis of methyl-substituted xanthotoxol to clarify prooxidant effect of methyl on radical-induced oxidation of DNA. Eur. J. Med. Chem. 2010, 45:2559-2566. 10.1016/j.ejmech.2010.02.044.
24. Domínguez M., Avila J.G., Nieto A., Céspedes C.L. Anti-inflammatory activity of Penstemon gentianoides and Penstemon campanulatus. Pharm. Biol. 2011, 49:118-124. 10.3109/13880209.2010.503708.
25. Mandel S., Youdim M.B.H. Catechin polyphenols: Neurodegeneration and neuroprotection in neurodegenerative diseases. Free Radic. Biol. Med. 2004, 37:304-317. 10.1016/j.freeradbiomed.2004.04.012.
26. Bastianetto S., Dumont Y., Han Y., Quirion R. Comparative neuroprotective properties of stilbene and catechin analogs: action via a plasma membrane receptor site?. CNS Neurosci. Ther. 2009, 15:76-83. 10.1111/j. 1755-5949.2008.00074.x.
27. Hou A.J., Peng L.Y., Liu Y.Z., Lin Z.W., Sun H.D. Gallotannins and related polyphenols from Pistacia weinmannifolia. Planta Med. 2000, 66:624-626. 10.1055/s-2000-8633.
28. Vaya J., Mahmood S. Flavonoid content in leaf extracts of the fig (Ficus carica L.), carob (Ceratonia siliqua L.) and pistachio (Pistacia lentiscus L.). Biofactors 2006, 28:169-175.
29. Compagnone R.S., Suarez A.C., Sciacovelli L., Delle Monache F. Arabinofuranoside flavonoids from Tapirira guianensis. Bol. Soc. Chil. Quim. 1997, 42:445-448.
30. Buchanan M.S., Carroll A.R., Fechner G.A., Boyle A., Simpson M., Addepalli R., Avery V.M., Forster P.I., Guymer G.P., Cheung T., Chen H., Quinn R.J. Small-molecule inhibitors of the cancer target, isoprenylcysteine carboxyl methyltransferase, from Hovea parvicalyx. Phytochemistry 2008, 69:1886-1889. 10.1016/j.phytochem.2008.04.011.
31. Vvedenskaya I.O., Vorsa N. Flavonoid composition over fruit development and maturation in American cranberry, Vaccinium macrocarpon Ait. Plant Sci. 2004, 167:1043-1054. 10.1016/j.plantsci.2004.06.001.
32. Kawashty S.A., Mosharrafa S.A.M., El-Gibali M., Saleh N.A.M. The flavonoids of four Pistacia species in Egypt. Biochem. Syst. Ecol. 2000, 28:915-917. 10.1016/S0305-1978(99)00113-1.
33. Marzouk M.S., Soliman F.M., Shehata I.A., Rabee M., Fawzy G.A., Flavonoids biological activities of Jussiaea repens. Nat. Prod. Res. 2007, 21:436-443. 10.1080/14786410600943288.
34. Nawwar M., Hussein S., Ayoub N., Hashim A., El-Sharawy R., Lindequist U., Harms M., Wende K. Constitutive phenolics of Harpephyllum caffrum (Anacardiaceae) and their biological effects on human keratinocytes. Fitoterapia 2011, 82:1265-1271. 10.1016/j.fitote.2011.08.014.
35. Niemetz R., Gross G.G. Gallotannin biosynthesis: β-glucogallin: hexagalloyl 3-O-galloyltransferase from Rhus typhina leaves. Phytochemistry 2001, 58:657-661. 10.1016/S0031-9422(01)00300-4.
36. Baratto M.C., Tattini M., Galardi C., Pinelli P., Romani A., Visioli F., Basosi R., Pogni R. Antioxidant activity of galloyl quinic derivatives isolated from P. lentiscus leaves. Free Radic. Res. 2003, 37:405-412. 10.1080/1071576031000068618.
37. Ieri F., Innocenti M., Andrenelli L., Vecchio V., Mulinacci N. Rapid HPLC/DAD/MS method to determine phenolic acids, glycoalkaloids and anthocyanins in pigmented potatoes (Solanum tuberosum L.) and correlations with variety and geographical origin. Food Chem. 2011, 125:750-759. 10.1016/j.foodchem.2010.09.009.
38. Yu D.Q., Chen Y., Liang X.T. Structural chemistry and biological activities of natural products from Chinese herbal medicines - Part II. Res. Commun. Mol. Pathol. Pharmacol. 2000, 108:393-436.
39. Xie Y., Zhao W., Zhou T., Fan G., Wu Y. An efficient strategy based on MAE, HPLC-DAD-ESI-MS/MS and 2D-prep-HPLC-DAD for the rapid extraction, separation, identification and purification of five active coumarin components from radix angelicae dahuricae. Phytochem. Anal. 2010, 21:473-482. 10.1002/pca.1222.
40. Avula B., Wang Y.H., Smillie T.J., Khan I.A. Determination of Shikimic acid in fruits of illicium species and various other plant samples by LC-UV and LC-ESI-MS. Chromatographia 2009, 69:307-314. 10.1365/s10337-008-0884-z.
41. Nakamura S., Li X., Matsuda H., Ninomiya K., Morikawa T., Yamaguti K., Yoshikawa M. Bioactive constituents from Chinese natural medicines. XXVI. Chemical structures and hepatoprotective effects of constituents from roots of Rhodiola sachalinensis. Chem. Pharm. Bull. 2007, 55:1505-1511. 10.1248/cpb.55.1505.
42. Hibi T., Aoki S., Oda K., Munemasa S., Ozaki S., Shirai O., Murata Y., Uozumi N. Purification of the functional plant membrane channel KAT1. Biochem. Biophys. Res. Commun. 2008, 374:465-469. 10.1016/j.bbrc.2008.07.026.
43. Fu S., Arráez-Roman D., Segura-Carretero A., Menéndez J.A., Menéndez-Gutiérrez M.P., Micol V., Fernández-Gutiérrez A. Qualitative screening of phenolic compounds in olive leaf extracts by hyphenated liquid chromatography and preliminary evaluation of cytotoxic activity against human breast cancer cells, Anal. Bioanal. Chem. 2010, 397:643-654. 10.1007/s00216-010-3604-0.
44. Redeuil K., Smarrito-Menozzi C., Guy P., Rezzi S., Dionisi F., Williamson G., Nagy K., Renouf M. Identification of novel circulating coffee metabolites in human plasma by liquid chromatography-mass spectrometry. J Chromatogr. A 2011, 1218:4678-4688. 10.1016/j.chroma.2011.05.050.
45. Ma W.H., He J.C., Duan P.S., Han T., Zheng C.J., Qin L.P. Dibenzocyclooctane lignans from the stems of Schisandra bicolor. Biochem. Syst. Ecol. 2010, 38:1156-1159. 10.1016/j.bse.2010.10.011.